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Resins for Solid Phase Peptide Synthesis

Date:2014-09-29

 SEPLITE®Chloromethyl resin (Merrifield resin)

Chemical structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB or 2%DVB
Loading: 0.5-4.0mmol/g

SEPLITE®Merrifield resin has in the past been the standard support for the synthesis of peptide acids by Boc strategy. Originally, the cesium salt of a protected amino acid was anchored to the chloromethyl support via nucleophilic displacement of chlorine. Although, Me4N salts, sodium salts in THF with Bu4NF catalysis and more recently Zinc salts in EtOH have also been used. Cleavage can be effected by treatment of resin with HF or TFMSA, by hydrogenolysis, and by treatment with trimethyltin hydroxide. Alcohols can be released using reducing agents such as diisobutylaluminium hydride or LiBH4. Methyl esters can be produced by transesterification with methoxide. Alcohols can be coupled to chloromethyl resin by heating together in DMF the resin and corresponding potassium

or sodium alkoxide.

 

 SEPLITE®4-Benzyloxybenzy Alcohol Resin (Wang resin)

Chemical structure:

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB or 2%DVB
Loading: 0.4-2.0 mmol/g

SEPLITE®  Wang resin is the most widely used of all resins for SPOS. As a standard support it can be used for the solid phase immobilization of acids and phenols for SPOS. The ester linkage may be achieved, which has good stability to a variety of reaction conditions, but can be readily removed with the moderate acid treatment, generally with trifluoroacetic acid. For the immobilization of amines, Wang resin also can be readily converted into solid phase equivalents of standard urethane-based protecting groups by reaction with phosgene or activated carbonates, such as carbonyl diimidazole or bis(p-nitrophenyl)-carbonate.

 

 SEPLITE®Aminomethyl resin

Chemical structure:

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB or 2%DVB
Loading: 0.4-2.0mmol/g

SEPLITE® Aminomethyl polystyrene resin is one of the most widely used functionalized supports for solid-phase synthesis. Many supports can be made by acylating this resin withy carboxylic acid-containing linkers using standard methods of amide bond formation to furnish supports for solid phase organic synthesis.

 

 SEPLITE® 4-methylbenzhydrylamine Hydrochloride Salt Resin (MBHA resin)

Chemical structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB
Loading: 0.3-1.6mmol/g

SEPLITE® MBHA resin is used in the synthesis of peptide amide by Boc SPPS. Carboxylic acids or amino acids can be attached using standard methods of amide bond formation. Cleavage of the carboxamides from MBHA resin can be achieved by treatment with HF or TFMSA. The excellent swelling properties of MBHA resin makes them ideal matrices onto which to attach linkers for combinatorial synthesis, although care must be taken to avoid strongly acidic conditions during synthesis, as this may result in some loss of linker.
MBHA resin has been also utilized to produce quinolinones from β-lactams, and recently used in solid phase synthesis of 2-arylaminobenzimidazoles, nucleic acid analog peptide.

 

 SEPLITE®2-Chorotrityl chloride resin

Chemical  structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB
Loading: 0.4-1.6mmol/g

SEPLITE®2-Chorotrityl chloride resin is a very acid sensitive resin suitable for the synthesis of protected peptide fragments by the Fmoc strategy. In particular, it’s suitable for the preparation of C-terminal prolyl and cysteinyl peptides. Cleavage from this resin is achieved by using 1-95% TFA in DCM (containing 8% triisopropylsilane), AcOH/CF3OH/DCM, 0.5% TFA or hexafluoroisopropanol. Recently, this resin has been used in cyclization reactions under Heck reaction conditions, the solid phase synthesis of β-peptides via the Arndt-Eistert homologation of Fmoc-protected amino acid diazoketones and in Mannich reactions of alkynes, secondary amines and aldehydes in the presence of a copper salt affording the corresponding aminomethylalkynyl adducts.
This resin can also be used in Fmoc peptide synthesis. Carboxylic acids can be released under very mild acidic conditions by treatment with AcOH/TFE/DCM or HFIP in DCM. Completely protected peptides are generated under these conditions.

 

 SEPLITE®4-(2’,4’-Dimethoxyphenyl-Fmoc-aminomethyl)-phenoxymethyl resin (Rink Amide resin)

Chemical structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB
Loading: 0.3-1.0mmol/g

SEPLITE®Rink amide resins are the standard supports for the production of primary carboxamides and sulfonamides by solid phase synthesis. Following removal of the Fmoc group (if present), the resin-bound amino group can be acylated using standard methods of amide bond formation. The resulting amide group is stable to a wide range of reaction conditions but is easily cleaved from the resin by treatment with 95% TFA. Reductive alkylation of the resin-bound amine, prior to acylation, provides a facile route to secondary carboxamides, whereas cleavage with trifluoroacetic anhydride leads to the direct release of nitriles.

 

 SEPLITE®Rink Amide-AM resin

Chemical structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB
Loading: 0.3-1.0 mmol/g

SEPLITE®resin is similar to the Rink Amide-MBHA resin, but it has a narrower range of chemical compatibility than the latter resin. It is also less sensitive to the standard 95% TFA cleavage reaction than Rink Amide resin.

 

 

 SEPLITE®Rink Amide-MBHA resin

Chemical structure:

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB
Loading: 0.3-1.0 mmol/g

 

 SEPLITE®4-(2’,4’-Dimethoxyphenyl-hydroxymethyl)-phenoxymethyl resin (Rink acid resin)

Chemical structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB
Loading: 0.3-1.2mmol/g

SEPLITE®Rink acid resins are super acid-labile supports for the solid phase immobilization of carboxylic acids. Cleavage can be effected with as little as 10%AcOH in DCM, providing highly acid-sensitivity products in high yields and purities. However, care must be taken to prevent product loss during synthetic manipulations, owing to the extreme acid sensitivity of this support. Treatment with HCl in THF or Ph3PCl2 had been shown to efficiently convert this resin to the corresponding benzhydryl chloride, to which can be coupled a wide range of functional groups: hydroxylamines; alcohol, amines, acids and thiols. Rink acid resin has also been converted to a trifluoroacetate with TFA and used in a similar manner to immobilize amines, thiols, alcohols, and phenols. In a more detailed study, the same authors found 1M trifluoroacetic anhydride in 2,6-lutidine to give superior results with less degradation of the linker. Rink resin trifluoroacetate has also been used to prepare purines. Cleavage of amines and alcohols from this support has been carried out with either 5%TFA in DCM or 20%TFA in DCM; thiols were released with either 5%TFA in DCM or 95% aq. TFA.

 

 

 SEPLITE®Hydroxymethyl Resin

Chemical structure:

 

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking:1%DVB or 2%DVB
Loading: 0.5-3.0 mmol/g

SEPLITE®resins are alternatives to the corresponding chloromethylated resins (Merrifield resins) and ideal for the attachment of acids by esterification. Diacids can be attached with less crosslinking compared to Merrifield resins. Release of the carboxylic acid from the resin can be effected by treatment with HF, trifluoromethane sulfonic acid or hydrogenolysis.

 

 

 SEPLITE®9-Fmoc-Aminoxanthen-3-yloxy-polystyrene resin (Sieber amide resin) Sieber

Chemical structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB
Loading: 0.25-0.65 mmol/g

SEPLITE®Sieber amide resins are excellent acid-labile supports for the preparation of carboxamides by SPOS. Cleavage of carboxamides from these supports can be effected with only 1% TFA in DCM, making them ideal for the synthesis of particularly acid-sensitive compounds and of products retaining acid-sensitive protecting groups. These resins can be readily reductively alkylated to provide supports for the synthesis of secondary carboxamides. Such materials give higher yield than the analogous supports derived from Rink amide resin, owing to the lower steric hindrance about the resin-bound secondary amine.
Sieber amide resin has also been employed to produce protected peptide fragments in which the C-terminal carboxyl group is blocked as a hydromethylphenoxy-β-alaninamide ester. Reaction of polymer-supported imines derived from this support has been used in the SPOS of aminophosphonic acids, and treatment of resin-bound primary amides with trifluoroacetic anhydride has been shown to result in direct release of the corresponding nitrile.

 

 

 SEPLITE®Sulfonyl Chloride resin

Chemical structure

Description:
Particle size: 100-200mesh or 200-400mesh
Crosslinking: 1%DVB or 2%DVB
Loading: 1.0-3.0 mmol/g

SEPLITE®Sulfonyl Chloride resin is an equivalent to tosyl chloride and can be used in numerous applications. When this resin is treated with nucleophiles, a variety of polymer bound sulfonates can be created (e.g. sulfonyl azides, sulfonyl hydrazine) and subsequently used as polymeric supports, polymer bound reagents or n catalytic organic synthesis. Application in the “catch and release” strategy, where the resin catches a compound to form a polymer bound tosylate. Purifying the polymer bound tosylate by washing and subsequent treatment by a nucleophile, releases the target product from the resin. A typical application is to form polymer bound tosylates by loading alcohols to the resin. Treatment with nucleophiles like amines, imidazoles or thiols generates the corresponding sec. or tert. amines, alkylimidazoles or thioethers. This resin can also be used as scavenger for amines, hydrazines and other nucleophiles.

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TypeInfo: Ion exchange resin

Keywords for the information:Merrifield resin